


Regrets

by Erratus



Category: Supernatural
Genre: Fluff and Smut, M/M, Plot What Plot/Porn Without Plot, Smut, Top!Castiel
Language: English
Status: Completed
Published: 2019-11-02
Updated: 2019-11-02
Packaged: 2021-01-16 22:24:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,549
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21278711
Author URL: https://archiveofourown.org/users/Erratus/pseuds/Erratus
Summary: Castiel has, thus far, had sex with Dean a hundred and thirty seven times. He remembers each one. He doesn't regret a single instance, though he does sometimes have regrets about them.Just some Destiel smut. Pretty fluffy too.





	Regrets

Castiel has, thus far, had sex with Dean a hundred and thirty seven times. He remembers each one. He doesn't regret a single instance, though he does sometimes have regrets about them.

His first attempt, for example, was horribly clumsy.

"Gentle!" Dean hissed when Castiel grabbed at his swollen bulge. He flinched and squirmed away, the exact opposite of what Castiel was hoping for.

"Sorry. It is hard to gauge the pressure they used in the videos," Castiel explained. He tried again, pressing against the hot mass and palming it. This time Dean groaned and pressed into his hand.

"Dude, no. No, no, no, porn isn't instructional," Dean seemed legitimately concerned. Castiel wasn't happy with the idea that all his research was invalid. "Have you ever done this before?" He asked. Castiel still had a hand on him but Dean seemed more interested in his answer.

"No. I am not interested in copulating with anyone else."

"What a romancer," Dean laughed. Castiel didn't know why it was romantic or if that was sarcasm. All in all, he was feeling dejected and put off.

"I'm sorry if my experience level is-"

"Hey it's okay. We all start somewhere. And luckily for you, I'm a pro at this," Dean was smiling again and rolling his hips into Castiel's hand. Suddenly the atmosphere was calmer and a new tension started to form in his gut.

"I will follow your direction. I'll follow you anywhere, Dean," Castiel sighed into the side of Dean's face.

"Hey, don't get sappy on me. This is sex, not some chick flick," Dean scolded. But his hands were alive, moving and touching Castiel. His fingers left hot trails over his flesh, but it wasn't nearly enough. The touches were light and through his clothes. Castiel also had the distinct feeling that there were better places to be touched than his back and side.

"I want you naked," Castiel announced.

"Let's take it slow. The build up is half the fun," Dean chuckled into his throat. Then his mouth was on his neck, teasing the flesh, his tongue and teeth- oh, it was good.

His hips bucked forward, seemingly seeking out precious friction. They ground against Dean's, his clothed dick rubbing against Dean's hot bulge; it was good, so good, exactly what he needed.

"Jesus, you're like a horny teen," Dean shoved him away. Castiel let him, though an undignified whine escaped his throat.

"I am as old as-"

"Yeah, you're an old dude, I got that. But you're also a virgin about to come in your pants." Truthfully Castiel couldn't say how close or far he was from orgasm so perhaps Dean was right. "Here, let me show you how this works," Dean muttered and returned to working on Castiel's neck. His nimble hands had both pairs of pants down within moments. His skin was hot as their erections brushed together, and Castiel finally understood the intimacy. He kissed Dean deeply on the lips, relishing in the moment.

Dean's hand wrapped around Castiel's dick and began working him. Slow pumps with small squeezes at the base and head. Their chests pressed together, his free hand handled Castiel’s balls and pressed on the sensitive skin just behind them.

"Is this what you wanted?" Dean asked him with a husky voice in his ear. Something snapped and Castiel's vessel seemed to act on its own. He rammed his lips into Dean's in a harsh kiss with teeth clashing. His hips thrust into Dean's hand and he gripped Dean's erection. He mimicked the way that Dean touched him. He felt Dean groan into the kiss and his hips buck. Something happened to Castiel. Something good, something great. Pleasure filled Castiel and he wanted more of Dean.  _ Dean Dean Dean _ . It was the only word running through his mind.

He wasn't entirely sure how long it lasted. When he came down he was panting into Dean's chest. Both of their hands were still and there was a new wetness dripping down them.

"And that was your first orgasm. How did you like it?" Dean laughed, resting a hand on his back. It was… good. It wasn't bad, absolutely not. But it could have been more. Castiel didn't regret the act, not really. He regretted not doing enough.

…..

Dean taught him the art of making love. Where to touch, how hard, when. Castiel was a fast learner. He was eager. Too eager. He regretted the first time he was inside Dean. Not that he got the opportunity. No, he cherished every time he got to be inside Dean. Rather, he regretted how the first time happened.

"Can you be the  _ delicatus _ ?" Castiel asked. The room was dark and they had already spent too long kissing on the bed. Their clothes were ruffled and misplaced, but still on their bodies. Heat ran through Castiel, a familiar need tight in his groin. He rutted up again Dean, grinding their bulges together, and laid wet kisses on Dean's neck.

"The… what?"

"The bottom," Castiel continued to rain kisses on him. "The Romans had better words for it."

"Oh." Dean's hands fell to the side. Castiel pulled away. "Yeah, uh, I don't normally… do that."

"Do you not trust me? To pleasure you how you pleasure me?" Castiel's fingers worked his top off. His flesh was soft and giving under his hand. He wanted Dean to writhe in pleasure, make his soul sing with joy.

"You know what? Fuck it. Let's do it. But just… be careful," Dean relented. Castiel's breath hitched and he thrust his hips.

"I will be," he promised and returned to undressing his lover. Thei kissing resumed in full. Shirts fell to the ground, followed by pants. Castiel's penis throbbed with excitement. He began stroking Dean, relishing in the wetness welling at the tip.

Castiel sat up, straddling Dean's thighs. His cock was rigid and dripping onto his belly. Castiel’s dick landed on Dean’s thigh, also straining. Dean cocked a brow at his gaze and grinned.

“Like what you see?” He asked with a blend of humor and seduction.

“Yes,” Castiel leaned down again to kiss him. He wanted to say that he always cherished their intimate times. That he loved him. That he knew that Dean loved him back, even if he never said it. He would be careful, and pour all his love into this act. He loved that Dean wanted to have him like that. But that would be a ‘chick flick moment’, and Dean wouldn’t appreciate the words. So Castiel would show him with his actions.

He reached through space for the lube. He didn’t normally use his powers for frivolous matters, but he couldn’t be bothered to leave Dean’s side. Dean’s eye’s flickered with unease but Castiel was kissing him again. He could feel Dean relax under him, trust him. It was another cherished moment.

He used the lube as Dean had done on him many times before. He smeared it along his fingers and clenched his hand, warming it. He rubbed Dean’s hole, careful not to press in, not yet.

“You don’t have to do this,” Castiel murmured into his ear. He wanted Dean to want it. Dean had to want it.

“I want to,” Dean assured him and captured his lips to stop him from talking. Castsiel pressed a finger in and Dean hissed.

“Relax,” he could feel the tension release from Dean with a single breath. When he decided the muscles around his finger were loose enough, another finger pressed in. Dean stayed relaxed, though he had a pensive look and refused to make eye contact. Castiel searched out for his prostate, knowing first hand how quickly it could change the experience. 

Dean squirmed and gasped when he found it. His cock twitched with interest and Castiel continued to work it.

“Took you long enough,” Dean muttered. His face and chest were flushed and Castiel realized he needed to hurry things along. Dean might be able to hold on for a while, but Castiel still had to work on his stamina. He hoped that Dean was ready as he pulled his fingers out, hand away, and positioned himself. Dean’s knees fell around him and they aligned themselves hip to hip. Castiel worked a generous amount of lube onto his shaft.

“We should have done this sooner. It’s pretty hot,” Dean commented, staring hungrily at their hips.

“We can do this more often,” Castiel muttered his agreement. He lined himself up and pressed forward, slowly, carefully. He remembered all the times that Dean entered him, how it felt. He compared it to how he felt then, pressing in. The tightness, warmth, and deeper feeling of claiming his lover was overwhelming. He wanted to move, to snap his hips and bite and kiss and  _ make Dean his _ . He stifled all those needs into a pleased whimper and small hip movements.

“Jesus Cas, you…” His sentence ended with a moan. Castiel started to fondle Dean’s dick, slowly and carefully. It was more about distracting him from the pain than anything. Something that Dean had done for him before.

“Dean, can I? Please?” Castiel begged. He needed to move. He needed to thrust and  _ feel _ . He couldn’t simply stay still any longer.

“Yeah, yeah. I think I’m good,” Dean’s hand curled around his neck. They pulled in for another kiss as his hips started to work. In and out. The tight ring of muscle moving around him. The warmth and cold and warmth again. Castiel’s head rolled from side to side. He wanted more. He needed more. To needed to make Dean  _ his _ . Have him writhe with pleasure, beg for me, understand their connection.

His hips moved faster, harder, Dean hissed and wiggled under him.  _ More more more _ . It was his only thought as their hips slammed together. A hand landed on his chest.

“Cas! Slow down, will you?” Dean said sharply. There was no pleasure, no need in his voice. Just the small tremor of pain. Cas stopped and looked down at Dean. He tried to hide it, but he could see the pain on his face. The short, sharp breaths. His gaze looked to the side, almost ashamed. Maybe afraid. The thought made Castiel freeze.  _ He was hurting Dean _ .

“I’m sorry, I didn’t…” Mean to. Want to. Realize. Excuses ran through his head. Excuses for hurting Dean in the most intimate of moments.

“Cas, it’s okay. I get it. You got carried away. Trust me, I’ve been in your shoes.” Dean reached out and grabbed his hand. He could feel the movement around him; he was still inside Dean. Despite the disgust for himself, his cock still happily throbbed with the sensation. 

“Dean, I said I wouldn't hurt you,” he muttered. He wanted to pull out. To stop. He failed Dean in the worst possible way. Dean just shook his head. Suddenly their chests were pressed together and their positions flipped. Dean was on top, Castiel still half inside him.

“How about this. I bottom, from the top,” Dean offered. Humor and lust and want filled his voice again. He slid down and Castiel was suddenly buried deep inside. An ‘oh’ might have escaped him, he could not be certain. “Sound good?” Dean probed. His hips were rocking gently, swaying so delicately. He bit his lower lip in pleasure. His eyes smoldered and Castiel could feel him move around him.

“Yes. Please. I don’t want to hurt you,” Castiel cupped his face. A silent apology that was forgiven before it was even spoken. Dean rocked harder into him and groaned happily. Castiel’s hands were on his hips. He felt the need for  _ more harder faster need more _ crept in, but his hips only moved modestly. Dean did most of the work, riding his cock with growing enthusiasm. Soon his hand was around his cock, pumping in time.

“Really need to… more often…” he grunted, lost in lust. Castiel’s back arched and his toes curled. Dean was all around him, moving harder and faster. His green eyes were sharp with lust and Castiel could feel the enjoyment rock through him. The enjoyment that he was giving him. The enjoyment from having Castiel inside him.

Castiel’s hips snapped up, only once, as he came. His hands, still tight on Dean’s hips, forced him deep inside. He cried Dean’s name and words in dead languages, praises to his father as he spilled his hot seed inside Dean. Dean’s hand was pumping harder, faster, and a moan fell from his lips. Semen spilled across his stomach as Dean’s own orgasm crested.

Castiel relaxed his grip on Dean’s hips. His hands slipped around, revealing red prints on each hip. They would bruise into blotches that resembled hand prints. Part of Castiel crumbled at the notion of hurting Dean during their intimate moments. Another part relished in leaving his mark.  _ Mine _ . How many of his hand prints could he plaster onto Dean?

“I’m sorry,” Castiel apologized.

“Shut up already,” Dean accepted.

…..

There were more mundane reasons for Castiel to regret sex. Like when he had Dean; dick in mouth. He was kissing and licking and sucking. He switched to lazy pumps of his hand and wet kisses on the inner thigh. It was a slow, teasing blowjob. Castiel enjoyed making Dean unravel.

“God Cas, please,” Dean tried to buck his hips. Castiel’s hand kept them firmly in place. He pulled his head back, releasing Dean’s dick with an audible  _ pop _ .

“In time,” he said. He went back to using his hand. The pace and rhythm were intentionally not enough to make Dean come. “How do you want it?” He asked after a minute. He punctuated his question with a long lick up the bottom on Dean's shaft.

“In your mouth, your ass, your stomach. God, I don’t care, just get me off,” Dean begged. His cock twitched with need. Castiel smiled, liking the answer. He could have Dean however he wanted, whenever he wanted.

_ Cas! I kind of need some backup. Right fucking now! _ Sam’s voice rang through him. He pulled back and his hands stopped, leaving Dean completely unattended.

“Cas?” It came out more as a whimper. Cas frowned and bite his lip.

“Sam needs me. Sounds urgent,” he confessed. His own cock throbbed with need. Before he had the promise of Dean to get him off, but the thought of appearing in front of Sam and whatever it was they were hunting wasn’t exactly exciting.

“Fuck,” Dean breathed. “Well, go to him. I can handle myself,” Dean’s hand moved to his own dick and held it tight. Castiel scowled. He didn’t work Dean up so much for him to masturbate in the shower. More importantly, he didn’t do all this to smite monsters while fully erect. 

“Wait twenty minutes. Maybe it’ll be fast,” Castiel stood and sent a pleading look at Dean. Dean just wandered into the bathroom.

“No can do. I was about ready to blow anyway,” he answered before he shut the door. Castiel frowned but decided to get to Sam before he died. Too bad it left both Castiel and Dean sexually frustrated. Castiel even more so. Though, all in all, he still didn’t regret it. 

Castiel didn’t regret a single time he had sex with Dean Winchester.

  
  


**Author's Note:**

> Thanks to Spaceboundwitch for beta reading this. Please leave a comment if you liked it, it keeps us motivated to write more.


End file.
